[17(20) E]- and [17(20) Z]-pregna-5,17(20)-dien-21-oylamides. Facile synthesis and primary evaluation for cancer cells proliferation

Reaction of 17α-bromo-21-iodo-3β-acetoxypregn-5-en-20-one with ammonia, primary, and secondary amines is simple and convenient method for preparation of [17(20) E]- and [17(20) Z]-pregna-5,17(20)-dien-21-oylamides. Synthesis and characteristics of 12 related amides are presented. Primary testing on...

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Veröffentlicht in:	Bioorganic & medicinal chemistry letters 2010-09, Vol.20 (18), p.5495-5498
Hauptverfasser:	Stulov, Sergey V., Zavialova, Maria G., Mehtiev, Arif R., Novikov, Roman A., Tkachev, Yaroslav V., Timofeev, Vladimir P., Misharin, Alexander Yu
Format:	Artikel
Sprache:	eng
Schlagworte:	Ammonia Androgens - metabolism Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Breast Neoplasms - drug therapy Cancer cells proliferation Carcinoma - drug therapy Cell Line, Tumor Cell Proliferation - drug effects Female Humans Male Pregnenolone - analogs & derivatives Pregnenolone - chemical synthesis Pregnenolone - pharmacology Pregnenolone derivatives Prostatic Neoplasms - drug therapy Synthesis
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Zusammenfassung:	Reaction of 17α-bromo-21-iodo-3β-acetoxypregn-5-en-20-one with ammonia, primary, and secondary amines is simple and convenient method for preparation of [17(20) E]- and [17(20) Z]-pregna-5,17(20)-dien-21-oylamides. Synthesis and characteristics of 12 related amides are presented. Primary testing on cells proliferation indicated differing effects of synthesized compounds on androgen insensitive MCF-7 cells and androgen sensitive LNCaP cells.
ISSN:	0960-894X 1464-3405
DOI:	10.1016/j.bmcl.2010.07.075